Reaktion #43250

Reaktionsgleichung

HCl

lithium aluminium hydride

Ethyl 3-bromo-4-methylbenzoate

Ethyl 3-bromo-4-methylbenzoate

LAH

ether

→

(3-bromo-4-methylphenyl)methanol

Ausbeute 90.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 1 hour
2. 2
   WaschenSeparate fractions and wash aqueous phase with ether (50 mL)
3. 3
   Trocknendried over magnesium sulfate
4. 4
   SonstigeSolvent removal
5. 5
   workup.WAITleft a clear oil

Vorschrift

Ethyl 3-bromo-4-methylbenzoate was reduced follows: 2 equivalents lithium aluminium hydride (LAH) in THF was cooled to 0° C. Ethyl 3-bromo-4-methylbenzoate in anhydrous THF (10 mL) was added slowly to the cooled solution of LAH over 10 minutes, while stirring. The mixture was stirred at room temperature for 1 hour. The reaction was cooled to 0° C. and poured into ether (100 mL). The mixture was acidified by adding 1N HCl (aqueous) dropwise over 10 minutes. Separate fractions and wash aqueous phase with ether (50 mL). The fractions were combined and dried over magnesium sulfate. Solvent removal left a clear oil. The yield was 90%. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 7.5 (s, 1H) 7.2 (d, 1H) 7.1 (d, 1H), 4.6 (s, 2H) 2.3 (s, 3H).

Quelle